potassium hydroxide; ethanol

oxygen

1.1: zinc diacetate / methanol; dichloromethane / 2 h / Darkness 2.1: potassium tert-butylate / tetrahydrofuran; tert-butyl alcohol / 72 h / Darkness 2.2: 14 h / Darkness 3.1: hydrogenchloride; water / 6 h / 20 °C 4.1: sodium amalgam; potassium hydroxide / 0.08 h / 80 °C / Darkness 5.1: recombinant oxygen-independent coproporphyrinogen III oxidase; [14C]-Ademetionine; Reduced nicotinamide-adenine dinucleotide; threo-1,4-dimercapto-2,3-butanediol / 1 h / 37 °C / pH 7 / Inert atmosphere; Bis-Tris buffer; Enzymatic reaction 5.2: 0.25 h / Bis-Tris buffer View Scheme

1.1: toluene-4-sulfonic acid / dichloromethane / 16 h / 20 °C / Darkness 1.2: 10 h 1.3: 14 h / Darkness 2.1: zinc diacetate / methanol; dichloromethane / 2 h / Darkness 3.1: potassium tert-butylate / tetrahydrofuran; tert-butyl alcohol / 72 h / Darkness 3.2: 14 h / Darkness 4.1: hydrogenchloride; water / 6 h / 20 °C 5.1: sodium amalgam; potassium hydroxide / 0.08 h / 80 °C / Darkness 6.1: recombinant oxygen-independent coproporphyrinogen III oxidase; [14C]-Ademetionine; Reduced nicotinamide-adenine dinucleotide; threo-1,4-dimercapto-2,3-butanediol / 1 h / 37 °C / pH 7 / Inert atmosphere; Bis-Tris buffer; Enzymatic reaction 6.2: 0.25 h / Bis-Tris buffer View Scheme

1.1: trifluoroacetic acid / 0.5 h / 0 °C 1.2: 0.33 h / 0 °C 2.1: toluene-4-sulfonic acid / dichloromethane / 16 h / 20 °C / Darkness 2.2: 10 h 2.3: 14 h / Darkness 3.1: zinc diacetate / methanol; dichloromethane / 2 h / Darkness 4.1: potassium tert-butylate / tetrahydrofuran; tert-butyl alcohol / 72 h / Darkness 4.2: 14 h / Darkness 5.1: hydrogenchloride; water / 6 h / 20 °C 6.1: sodium amalgam; potassium hydroxide / 0.08 h / 80 °C / Darkness 7.1: recombinant oxygen-independent coproporphyrinogen III oxidase; [14C]-Ademetionine; Reduced nicotinamide-adenine dinucleotide; threo-1,4-dimercapto-2,3-butanediol / 1 h / 37 °C / pH 7 / Inert atmosphere; Bis-Tris buffer; Enzymatic reaction 7.2: 0.25 h / Bis-Tris buffer View Scheme

1.1: trifluoroacetic acid / 3 h / 0 °C 2.1: toluene-4-sulfonic acid / dichloromethane / 16 h / 20 °C / Darkness 2.2: 10 h 2.3: 14 h / Darkness 3.1: zinc diacetate / methanol; dichloromethane / 2 h / Darkness 4.1: potassium tert-butylate / tetrahydrofuran; tert-butyl alcohol / 72 h / Darkness 4.2: 14 h / Darkness 5.1: hydrogenchloride; water / 6 h / 20 °C 6.1: sodium amalgam; potassium hydroxide / 0.08 h / 80 °C / Darkness 7.1: recombinant oxygen-independent coproporphyrinogen III oxidase; [14C]-Ademetionine; Reduced nicotinamide-adenine dinucleotide; threo-1,4-dimercapto-2,3-butanediol / 1 h / 37 °C / pH 7 / Inert atmosphere; Bis-Tris buffer; Enzymatic reaction 7.2: 0.25 h / Bis-Tris buffer View Scheme

1.1: toluene-4-sulfonic acid / dichloromethane / 16 h / 20 °C / Darkness 1.2: 10 h 1.3: 14 h / Darkness 2.1: zinc diacetate / methanol; dichloromethane / 2 h / Darkness 3.1: potassium tert-butylate / tetrahydrofuran; tert-butyl alcohol / 72 h / Darkness 3.2: 14 h / Darkness 4.1: hydrogenchloride; water / 6 h / 20 °C 5.1: sodium amalgam; potassium hydroxide / 0.08 h / 80 °C / Darkness 6.1: recombinant oxygen-independent coproporphyrinogen III oxidase; [14C]-Ademetionine; Reduced nicotinamide-adenine dinucleotide; threo-1,4-dimercapto-2,3-butanediol / 1 h / 37 °C / pH 7 / Inert atmosphere; Bis-Tris buffer; Enzymatic reaction 6.2: 0.25 h / Bis-Tris buffer View Scheme

1.1: palladium 10 on activated carbon; hydrogen / methanol / 20 h / 20 °C 2.1: trifluoroacetic acid / 3 h / 0 °C 3.1: toluene-4-sulfonic acid / dichloromethane / 16 h / 20 °C / Darkness 3.2: 10 h 3.3: 14 h / Darkness 4.1: zinc diacetate / methanol; dichloromethane / 2 h / Darkness 5.1: potassium tert-butylate / tetrahydrofuran; tert-butyl alcohol / 72 h / Darkness 5.2: 14 h / Darkness 6.1: hydrogenchloride; water / 6 h / 20 °C 7.1: sodium amalgam; potassium hydroxide / 0.08 h / 80 °C / Darkness 8.1: recombinant oxygen-independent coproporphyrinogen III oxidase; [14C]-Ademetionine; Reduced nicotinamide-adenine dinucleotide; threo-1,4-dimercapto-2,3-butanediol / 1 h / 37 °C / pH 7 / Inert atmosphere; Bis-Tris buffer; Enzymatic reaction 8.2: 0.25 h / Bis-Tris buffer View Scheme

hydrogenchloride; iron(II) sulfate

1: With recombinant oxygen-independent coproporphyrinogen III oxidase; [14C]-Ademetionine; Reduced nicotinamide-adenine dinucleotide; threo-1,4-dimercapto-2,3-butanediol T=37°C; pH=7; 1 h; Inert atmosphereBis-Tris bufferEnzymatic reaction; 2: With dihydrogen peroxide 0.25 h; Bis-Tris buffer;